Your first 90 days as an Executive Assistant: what to do in weeks one, four and twelve

The first ninety days in a new Executive Assistant role are when your executive decides, often without really noticing, how much to trust you with, and I think that makes them some of the most important days of the whole partnership. I spent fifteen years as a senior EA in FTSE 100 chief executive offices and then managed a global team of 60 EAs, and in my experience the people who flourish aren’t always the most experienced. They tend to be the ones who listen before they speak, who keep looping back even when it would be easier not to, and who tell their executive what they’ve understood before being asked. I’d like to share what I would do in week one, week four and week twelve.

Week one: understand before you prove

Most of us arrive in a new role wanting to prove ourselves, which is completely understandable, but I would encourage you to arrive wanting to understand. That might sound a little soft, although it’s the most practical advice I can give you, because everything you do in your first month is read as a signal of how you will behave a year from now.

In the first two days, I would simply watch. Notice how your executive works, including their rhythm, how they like to receive information, and when their energy is high and when it drops, and please don’t assume you know the culture yet, even if you have done this job three times before. On days three and four, take on something manageable, deliver it well and then tell them it’s done, because reliability is built in small, visible moments. By day five, ask one good question that shows you have been paying attention, such as “I noticed the Thursday meeting always overruns. Is that something you’d like me to take ownership of?”

At the end of the week, write down privately what you’ve learnt and what you’re still guessing about. Nobody but you ever needs to see it, and I think you’ll find it becomes the most useful thing you own in your first three months.

Week four: the thirty-day email

If I could ask every new EA to do one thing, it would be this, because I did it myself and it changed the partnership. When I joined Lily’s recruitment business, our sister company Lily Shippen, I sat quietly for the first month, asked open questions and absorbed everything, from the priorities and relationships to the pressure points and the things left unsaid. At thirty days I sent Lily an email presenting back what I had understood. It wasn’t a status update, it was closer to “Here is what I think matters most to you, here is how I think you work, here is what I believe my job is, am I right, and what have I missed?”

Lily still says it was one of the most useful things anyone had done, and I would recommend it to EAs at every level, because the email does several things at once. It shows your executive that you have been listening, it gives them an easy way to correct your understanding before a wrong assumption costs either of you anything, and it quietly moves you from someone who takes instructions to someone who holds the picture.

I would keep it short enough to read on a phone, with four parts covering what you understand about their priorities, what you understand about how they like to work, what you think your role is, and the two or three questions you still have. Then ask for twenty minutes to talk it through.

Weeks five to eight: loop back

Once the first month is behind them, many EAs stop asking the questions they asked at the start, whereas the people who build exceptional partnerships keep looping back as a discipline, even when nothing has gone wrong. You might ask “Are my priorities still matching yours?”, “You mentioned the restructure in my first week. Is that still live?” or “Is there anything you’d like me to do differently?” An executive once told Lily about a partnership that had quietly failed because three things that mattered to the executive had been briefed in week one and never mentioned again, and nobody had looped back, which is exactly the gap you’re closing.

Week twelve: the shift from reactive to proactive

The first sixty days will be reactive to some degree (of course they will, you are learning!), but by about day sixty-one, the best EAs change gear. Being proactive doesn’t have to mean doing more, because it’s really about doing the right things before they become urgent, and there are three places I would start.

Firstly, look at the diary six to eight weeks out rather than two, and ask what each big moment needs before it arrives. Secondly, protect your executive’s capacity, which means declining politely, stopping meeting creep and building in time to think, because most senior people are over-committed and an EA who manages their energy as well as their time becomes essential. Thirdly, when you flag a problem, bring a suggestion with it. Each of these takes something off your executive’s mind and shows the quality of your judgement, which is where I think the real value of the role sits.

Then, at ninety days, write a second email. This one looks forward rather than back, covering what has been delivered, what is still in motion and where you would like to grow next quarter, with one question at the end, which is what your executive would most value from you from here. I would ask for a proper conversation about it, and if you’ve written the first email, you’ll find the second one much easier to write.

If you are the executive

This only really works when both people show up, so there is a lot you can do to help. In the first two weeks, give your EA the context they can’t find anywhere else, such as your real priorities rather than the job description, the relationships that matter and the ones that are complicated, how you like to communicate, what you find tiring and what frustrated you about the last arrangement. Then please be available in the first month, even if it’s only fifteen minutes three times a week, because every minute you spend aligning in week one will save you hours in month three.

Where the guide comes in

Lily and I wrote all of this down properly, because a blog post can give you the shape of the first ninety days but not the working tools. The First 90 Days: the complete guide is a 59-page working companion with the full week-by-week plan, the 60 and 90-day emails written out, the intelligence map you build from your first week, a private self-review for the ninety-day conversation, and a section written for your executive that you can hand over on day one. It costs £39 including VAT and you keep it.

Once you’ve settled in, the EA & PA Strategy Training Day is a natural next step, and if you would like to talk your first ninety days through with me first, I would be very happy to do that on a free discovery call. If you are still at the application stage, Lily has written about how to write an executive assistant CV that gets you interviews, and it is well worth reading before you apply.

The guide for this: The Executive Partnership Review (£25 including VAT) is for the next stage, once you are in: reviewing the partnership with your executive, agreeing decision rights and improving one thing at a time. It is one of the eavolve Coaching Guides, written by Emily Partridge and Lily Shippen.

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